Quadricyclonon-8-ene and its production



United States Patent Ofiice quadricyclo (2.2. l .2 .0 )nonanes is known in the art, being produced by condensation of bicyclo(2.2.1)hepta-2,5-diene with certain ethylenic compounds activated by the presence of an electron-withcarbon atom which is a member of the ethylenic linkage. For example, Schrauzer, Chem. Ber., 95, 2764 (1964), discloses the production of an 8 cyanoquadricyolo(2.2.l.2 .0

been available.

It is an object of the present invention to provide the novel compound quadricyclo(2.2.1.2 .0 )non-8-ene. An additional object is to provide a method for the production thereof.

It has now been found that these objects are accomplished by pyrolyzing heXacycl(7.2.1.l. .l .0 .0 tetradec-lO-ene at certain elevated temperatures.

The precursor employed is the hexacyclotetradecene represented by the formula wherein the added method not dependent, however, upon utilization of any particular stereoisomen'c form.

The hexacyclotetradecene reactant is converted to the desired quadlicyclononene by pyrolysis at temperatures from about 300 C. to about 600 C., although temperatures from about 400 C. to about 500 C. are preferred.

thermal conversion of the is conducted in a batchwise manner as by maintaining the hexacyclic reactant at an 3,350,463 Patented Oct. 31, 1967 elevated tempertaure therefrom as by distillation. In

through a heated tube, preferably employing an inert carrier gas such as helium, argon, nitrogen, steam or the like to facilitate passage through the reactor, and condensing the efliuent to afford selective extraction, selective adsorption and the like. The product of the invention is quadricyclo(2.2.1.2 .0 )non-8-ene which is depicted by the formula wherein the added numerals indicate one conventional method of identifying the relative locations of the carbon atoms present.

Although the novel quadricyclononene is useful as a el, it

To further illustrate the scribe the novel product thereof,

EXAMPLE I The reactor employed in this example was an unpacked rate of 22.4 mL/min. and a mixture dimers consisting of 94% of hexacyclo (7.2.1.1 .1 .0 .0 -tetradec-10-ene at the rate of 9.84 g./hr. (9 ml./hr.). The reactor was maintained at a temperature of 450 C. and the residence tadiene dimer was 89% nonene, based on the hexacyclotetradecene converted, was

From a similar run, a quantity of the quadn'cyclo- (2.2.l.2 .0 )-non-8-ene was isolated by distillation of the reactor efiiuent. The quadricyclonene is characterized by a freezing point of 35 1.007 g./ml. and a with the above formula.

I claim as my invention: 7 1. The process of producing quadricyclo (2.2.1.2 .0 non-8-ene by pyrolyzing hexacyclo(7.2.1.1 .1 .0 .0 )tetradec-lO-ene at a temperature of from about 300 C. to about 600 C. and recovering from the resulting product mixture said quadricyclononene.

2. The process of claim 1 wherein the temperature is from about 400 C. to about 500 C.

3. The compound quadricyc1o(2.2.1.2 .0 )non-8- ene.

References Cited UNITED STATES PATENTS 3,326,992 6/1967 Muller 260-666 FOREIGN PATENTS 1,186,052 1/1965 Germany. 1,197,083 7/1965 Germany.

OTHER REFERENCES DELBERT E. GANTZ, Primary Examiner. V. OKEEFE, Assistant Examiner. 

1. THE PROCESS OF PRODUCING QUADRICYCLO(2.2.1.2**3.5./**2.6) NON-8-ENE BY PYROLYZING
 3. THE COMPOUND QUADRICYCLO(2.2.1.23,50**2,6)NON-8ENE. 